Oliveto Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top hotels in Oliveto

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is S$832 per night from 21 Jul to 22 Jul
S$832
21 Jul - 22 Jul
includes taxes & fees
9.6/10 Exceptional! (212 reviews)
"Would definitely come back! The Italian garden at the property is beautiful."

Reviewed on 9 Jul, 2025

Villa di Piazzano - Small Luxury Hotel of the World
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
9.4/10 Exceptional! (233 reviews)
"We stayed here as a family of six, including our two 3-year-olds, and it was by far our favorite place during our time in Italy! The kids absolutely loved swimming in the pools and running around the beautiful property. It felt peaceful, safe, and perfect. The breakfast was lovely each morning—fresh, ..."

Reviewed on 28 Jun, 2025

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Castello di Spaltenna- Small Luxury Hotels of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is S$472 per night from 27 Jul to 28 Jul
S$472
27 Jul - 28 Jul
includes taxes & fees
9.8/10 Exceptional! (218 reviews)
A hidden gem
"Excellent service, very nice hotel"

Reviewed on 10 Jul, 2025

Monastero di Cortona Hotel & Spa
See all 5,235 properties in Oliveto
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

What to do in Oliveto

Tasting with Private Walk in a Cellar in Tuscany

Tasting with Private Walk in a Cellar in Tuscany

S$37
per adult
Tasting with Private Walk in a Cellar in Tuscany
The art of the Italian Aperitivo with a Cesarina in Arezzo

The art of the Italian Aperitivo with a local in Arezzo

S$157
per adult
The art of the Italian Aperitivo with a local in Arezzo
Wine Tasting: a SYRAH that makes you fall in love

Wine Tasting: a SYRAH that makes you fall in love

S$45
per adult
Wine Tasting: a SYRAH that makes you fall in love
See all activities in Oliveto

Frequently asked questions

How much does an Oliveto holiday package cost?
You'll find cheap prices on Expedia for your Oliveto getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your holiday to Oliveto costs.
What are the cheapest months to go to Oliveto?
Travel in the low or shoulder season and you're likely to find cheap Oliveto holiday packages. Remember that school holiday periods and local events and festivals can impact prices, so do some research before you go.
How many days is enough for Oliveto?
With a well-planned itinerary, you can easily hit the most popular Oliveto attractions in a handful of days. But if you want to discover hidden gems or go on day tours, consider booking your Oliveto holiday for longer.
How to find the best Oliveto package deals?
Start your search for an Oliveto package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Oliveto package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oliveto getaway off to a flying start.
Is it cheaper to book an Oliveto holiday as a package?
You can enjoy significant savings on your Oliveto getaway by booking a tailored holiday package. Check the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Oliveto?
If you have your Oliveto travel dates locked in, book as early as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Oliveto?

  1. Choose when to travel: Check your diary and pack your bags. Your favourite season and the activities on offer will also help you decide when to escape to Oliveto.
  2. Set your budget: Consider expenses like flights, meals and transportation when calculating how much to put aside for your trip to Oliveto. Then, choose a hotel that fits your budget, whether that's an affordable option or a more luxurious retreat.
  3. Decide your trip length: Consider how much time you want to spend discovering Oliveto. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick an Oliveto holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.